The Confident Indie Blog

Hi June-
Yours is the best indie tax site out there. Great Job.
My husband has a consulting business and we need to buy our own health insurance. Since health insurance has changed, I've found buying individual policies in our state PA may be a better way to go than family coverage. The [...]

June --
I am a self employed designer. My wife works full time at a large corporation. We buy health insurance for the whole family through the plan at her job. Can I write off as an expense any part of that?
Thanks!
Dennis
Print Designer
Columbia, SC
Current tax law, [...]

Hi June. Haven’t been on your site for awhile but didn’t see an obvious answer to this obvious question. How does the proposed healthcare law affect indies? I do some freelancing and also have a W2 job with no insurance benefits. So I have no insurance currently and haven’t for some time. Just pay [...]

June --
I noticed on the download I just received (quicken categories for the self-employed) that vitamins are listed as a deduction.
I am self-employed with a company that sells vitamins. I would love that this deduction is true because this would be a great selling point for all the business owners I [...]

Hi June,
I am recently retired as of July 2011 from a full time job.I now wish to work part time as a musician.
It appears that in NY Health insurance costs for myself and my wife are less for business people than individuals. Can you comment on this? Does this only apply [...]

June --
I am a Computer IT consultant 4 years. Just came back to being a contractor again after several years of W2. I have a TIN and a name but never did the LLC. At age 60 I am most interested in what structure will allow me to put away the most retirements money [...]

Hi,
I'm a freelance writer/consultant in San Francisco, finishing my taxes, and would greatly appreciate a small bit of help/clarification.
As a full-time freelancer with no employer health plan, can I deduct the full cost of my health insurance payments? I have no access to a partner's plan or COBRA.
Last year [...]

Hi June,
I like how you write, it's fresh and easy to understand.
I have a question. I'm considering quitting my job and working for myself doing free-lance technical writing at home. My big fear is the cost of health insurance. Any tips?
As a sole proprietor, can I deduct ALL my [...]

Take a look at the Small Business Times based in Milwaukee. Our representatives in congress are trying to help us indies with health insurance.
Self-employed need level playing field in health care
The "Equity for Our Nation's Self-Employed Act" (H.R. 3660) was recently introduced in the U.S. House of Representatives by U.S. Reps. [...]

Hello June,
I have a wonderful therapist who is very expensive! I understand that it's fine to deduct psychotherapy. Now this therapist also happens to be a great bodyworker, and occasionally he does bodywork and other kinds of body-oriented psychotherapy on me. Even though I know "massage" isn't deductible, I still deduct this. Is [...]

Freelancers Union has worked for a long time to bring its dental insurance nationwide, and now it's here! Freelancers in all 50 states will be able to get dental coverage (Freelancers Union usual eligibility requirements apply). [...]

Hi June,
I have some questions about deducting health insurance premiums:
Would COBRA payments qualify as health insurance premiums I can deduct as a an indie? (I am not talking about the personal deduction which must be 7.5% of income.)
If COBRA does not qualify, would another plan qualify given the fact [...]

June,
I have been a personal trainer for 2 years. I am a veteran working in the health/fitness industry and have needed alternative and out-of-pocket medical treatments (acupuncture, physical therapy, massage) for a service-connected orthopedic problem (for which I do have a disability rating).
Working with these other health care professionals has also [...]

I purchased a couple of books re: self employment taxes. I like yours (Self-employed Tax Solutions) because it’s written in plain language. The JK Lasser book (Small Business Taxes) appears to be writ…Linda Gordon

I recently bought your book, and wanted to tell you what you already know – it’s terrific. So many great common-sense features. In addition to my “indie” business, I’ve also been a tax preparer for an…James M. Beidler

I just purchased your book Self Employed Tax Solutions, and let me start by saying this is the first time I have written an email to an author. I’m only in the third chapter and am so happy about the …Dean Iodice

I read Self-employed Tax Solutions from cover to cover in about 3 days (I finished it today), and found it engaging and well written. That’s high praise for a book on taxes. I’ve read other tax books ……Paul Plamondon